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3,4,6-Tri-O-acetyl-2-(N-acetylacetamido )-1,2-dideoxy-o-Iyxohex- 1-enopyranose, an Acetamido-n-galactal Derivative, and the Mechanism of its Formation from 2-Acetamido-2-deoxy-D-galactose

N. Pravdić ; Department of Organic Chemistry and Biochemistry, »Ruder Bo§kovic« Institute, · Zagreb,-Yugoslavia
H. G. Fletcher, Jr. ; National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Public Health Service, U.S. Department of Health, Education, and Welfare, Bethesda, Maryland 20014, U.S. A.

Puni tekst: engleski pdf 11.661 Kb

str. 125-133

preuzimanja: 160



The structure of an unsaturated amino sugar derivative, formed
in low yield when 2-acetamido-2-deoxy-o-galactose _is treated with
boiling isopropenyl acetate containing a trace of p-toluenesulfonic
acid, and formulated as 1,4,6-tri-0-acetyl-2-(N-acetylacetamido)-
2,3-dideoxy-o-threo-hex-2-enopyranose(II) in an earlier publication,
has been re-examined. Through a series of steps, including
catalytic hydrogenation, the substance has been converted into a
compound with an NMR spectrum which shows it to be 3,4,6-tri-
0-acetyl-2-(N -acetylbenzamido )-1,5-anhydro-2-deoxy-o-tali tol (X).
This fact, together with a re-examination of its NMR spectrum,
show the unsaturated compound to be 3,4,6-tri-0-acetyl-2-(N··
-acetylacetamido)-1,2-dideoxy-o-lyxo-hex-l-enopyranose (III), a
derivative of 2-acetamido-o-galactal (VI). The yield of III from
2-acetamido-2-deoxy-o-galactose has been substantially improved
through isolation of . 2-acetamido-1,3,4 , 6-tetra-0-acetyl-2-deoxy-~-
o-galactopyranose (XIII) as an intermediate and III has been
obtained in crystalline form. Evidence for the mechanism of its
formation is presented.

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